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Chapter 18: Q22P (page 947)

Predict the products of the following reactions.

Short Answer

Expert verified

Cyclopentanone on treatment with hydroxylamine in acidic medium generates oxime. It is a condensation reaction and loss of water molecule is there. Oximes exists as thick liquids and are insoluble in water.

Oxime of cyclopentanone

Step by step solution

01

Explanation of part (a):

Cyclopentanone on treatment with hydroxylamine in acidic medium generates oxime. It is a condensation reaction and loss of water molecule is there. Oximes exists as thick liquids and are insoluble in water.

Oxime of cyclopentanone

02

Explanation of part (b):

The given reactant on treatment with hydrazine in acidic medium gives hydrazone as the product. This is a condensation reaction and loss of water molecule occurs as a result.

Hydrazone of 3,4-dihydronapthalen-1-one

03

Explanation of part (c):

Benzophenone on reaction with phenylhydrazone in acidic medium generates phenylhydrazine of benzophenone as the product. This reaction is condensation reaction and occurs with a loss of water molecule.

Phenylhydrazine of benzophenone

04

Explanation of part (d):

Cinnamaldehyde on reaction with semicarbazide in acidic medium leads to the generation of semicarbazone of cinnamaldehyde. It is a condensation reaction which occurs with a loss of water molecule.

Semicarbazone of cinnamaldehyde

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Most popular questions from this chapter

Show how you would accomplish the following synthesis.

(a) Acetphenone鈫� acetophenone cyanohydrin

(b) Cyclopentancarbaldehyde鈫� 2-cyclopentyl-2-hydroxyacetic acid

(c) Hexan-1-ol 鈫�2-hydroxyheptanoic acid

Show a complete mechanism for this equilibrium established in diethyl ether with HCl gas as catalyst.

Name the following ketones and aldehydes. When possible, give both a common name and an IUPAC name.

(a)CH3CO(CH2)4CH3 (b)CH3(CH2)2CO(CH2)2CH3 (c)CH3(CH2)CO(CH2)2CH3

(d)PhCOPh (e)CH3CH2CH2CHO (f)CH3COCH3

(g)CH3CH2CHBrCH2CH(CH3)CHO (h)Ph-CH=CH-CHO

(i)CH3CH=CH-CH=CH-CHO

(j) (k) (l)

2,4鈥�Dinitrophenylhydrazineis frequently used for making derivatives of ketones and aldehydes because the products (2,4鈥�dinitrophenylhydrazones, called 2,4鈥�DNP derivatives) are even more likely than the phenlyhydrazones to be solids with sharp melting points. Propose a mechanism for the reaction of acetone with 2,4鈥�dinitrophenylhydrazinein a mildly acidic solution.

Show how the following transformations may be accomplished in good yield. You may use any additional reagents that are needed.

(a) bromobenzene 鈫� propiophenone

(b) CH3CH2CN 鈫� heptan-3-one

(c) benzoic acid 鈫� phenyl cyclopentyl ketone

(d) 1-bromo-hept-2-ene 鈫� oct-3- enal
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